Xanthene-9-carboxylic acid → HCID 10765199, compound

HRID 370268

Reaction equation

HRID 370268 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9](OC(C)(C)C)=O)[CH2:5][CH2:4]1.[CH:16]1[C:29]2[CH:28]([C:30]([OH:32])=O)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.Cl.C(N=C=N[CH2:39][CH2:40][CH2:41]N(C)C)C.ON1[C:50]2[CH:51]=C[CH:53]=[CH:54][C:49]=2N=N1>CN(C)C=O.O.C(N(CC)CC)C>[CH:39]1([CH2:9][N:6]2[CH2:5][CH2:4][CH:3]([NH:2][C:30]([CH:28]3[C:29]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[O:21][C:22]4[C:27]3=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:32])[CH2:8][CH2:7]2)[CH2:40][CH2:41][CH2:53][CH2:54][CH2:49][CH2:50][CH2:51]1

Participants

8

Reactant 4

HCID 65736Xanthene-9-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 2756033tert-Butyl 4-aminopiperidine-1-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 10765199HCID 10765199, compoundYield 90.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

4.71 g of 4-amino-1-t-butoxycarbonylpiperidine hydrochloride and 4.50 g of xanthene-9-carboxylic acid were suspended in 150 ml of anhydrous N,N-dimethylformamide, and 5.5 ml of triethylamine was added thereto. The mixture was cooled in ice and 5.73 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter referred to as EDCI.HCl) and 4.04 g of 1-hydroxybenzotriazole were successively added thereto. The temperature was raised to room temperature immediately, and the reaction solution was stirred for 12 hours. After the reaction solution was cooled to 0° C., 80 ml of water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with 10% citric acid solution, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 7.78 g of the title compound as a white solid was obtained.

Workup

  1. temperatureThe mixture was cooled in ice
  2. additionwere successively added
  3. temperatureAfter the reaction solution was cooled to 0° C.
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with 10% citric acid solution, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  6. dry with materialby drying over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-182ba7e6140b439eb025aae22a13211e
Source dataset
uspto-grants-2000_10
Patent number
US06140338

Linked notes

Loading…